(R)-Benzyl 2-methyl-4-oxopiperidine-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl 2-methyl-4-oxopiperidine-1-carboxylate (1.97 g, 7.95 mmol) and 4′-(isopropylsulfonyl)biphenyl-2-amine (2.19 g, 7.95 mmol) in acetic acid (25 mL) was added trimethylsilyl cyanide (0.79 g, 7.95 mmol). After stirring the reaction at rt overnight the reaction was poured into an icy solution of ammonium hydroxide (30 mL). The solution was extracted with chloroform (three times), dried over MgSO4 and concentrated under vacuum. Purification by silica gel chromatography afforded the desired product. To enhance the cis/trans product ratio the isolated material was dissolve in methanol (20 mL) and trimethylsilyl cyanide (3.18 g, 23.9 mmol) was added. After stirring the reaction at 70° C. overnight the reaction was concentrated under vacuum. Purification by silica gel chromatography afforded the desired product. the reaction at rt overnight the reaction The solution was extracted with chloroform (three times) dried over MgSO4 concentrated under vacuum Purification by silica gel chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The crude Racemic benzyl 2-methyl-4-oxopiperidine-1-carboxylate was dissolved in MeOH and chromatographed on a 10 cm Chiralpak AD column eluting with 100% MeOH in 2.5 g injections to give the two separated enantiomers. The desired enantiomer eluted first, 95% ee. chromatographed on a 10 cm Chiralpak AD column eluting with 100% MeOH in 2.5 g injections to give the two separated enantiomers The desired enantiomer eluted first